Ethyl chloroacetate → 2-chloro-N-[1-(4-chlorophenyl)ethyl]acetamide

HRID 635151Notes

Reaction equation

HRID 635151 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13](OCC)=[O:14]>C(OC)(C)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:13](=[O:14])[CH2:12][Cl:11])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7751Ethyl chloroacetateHCID 978031-(4-Chlorophenyl)ethylamine

Product 1

HCID 35546952-chloro-N-[1-(4-chlorophenyl)ethyl]acetamide

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

At room temperature, a solution of 4.67 g (0.03 mol) of racemic 1-(4-chloro-phenyl)ethylamine in 40 ml of methyl tert-butyl ether is admixed successively with stirring with 5.5 g (0.045 mol) of ethyl chloroacetate and 0.4 g of Novozym 435® (=immobilized lipase from Candida antarctica; 7300 U/g). Stirring is continued at room temperature and the progress of the reaction is monitored by gas chromatographic sample analysis. After 1 hour, a conversion of 51% is reached. At this stage, the reaction is terminated by filtering off the enzyme. In the filtrate that remains, the (S)-enantiomer of 1-(4-chloro-phenyl)-ethylamine has an ee value of 89.1%, while the (R)-enantiomer of N-[1-(4-chloro-phenyl)-ethyl]chloroacetamide is obtained with an ee value of 95.5%.

Workup

  1. customAt room temperature
  2. customis continued at room temperature
  3. customAt this stage, the reaction is terminated
  4. filtrationby filtering off the enzyme

Sources & evidence

ORD record
ord-9a308f42024341588a452af7565e6cef
Source dataset
uspto-grants-2001_02
Patent number
US06187582B1

Reaction notes

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